CA1210387A - .beta.-LACTAM ANTIBIOTIQUE - Google Patents

.beta.-LACTAM ANTIBIOTIQUE

Info

Publication number: CA1210387A
Authority: CA; Canada
Prior art keywords: salt; isomer; penicillin; carboxy; isomerically enriched
Prior art date: 1982-10-15
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000438962A

Other languages

English (en)

Inventor

William J. Kerr

Dennis E. Clark

George Andreescu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Beecham Group PLC

Original Assignee

Beecham Group PLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1982-10-15

Filing date

1983-10-13

Publication date

1986-08-26

1983-10-13 Application filed by Beecham Group PLC filed Critical Beecham Group PLC

1986-08-26 Application granted granted Critical

1986-08-26 Publication of CA1210387A publication Critical patent/CA1210387A/fr

Status Expired legal-status Critical Current

Links

239000003782 beta lactam antibiotic agent Substances 0.000 title description 3
150000003839 salts Chemical class 0.000 claims abstract description 24
150000002960 penicillins Chemical class 0.000 claims abstract description 10
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 7
150000001768 cations Chemical class 0.000 claims abstract description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
238000000034 method Methods 0.000 claims description 32
239000000203 mixture Substances 0.000 claims description 27
229930182555 Penicillin Natural products 0.000 claims description 21
229940049954 penicillin Drugs 0.000 claims description 21
238000002425 crystallisation Methods 0.000 claims description 20
150000001875 compounds Chemical class 0.000 claims description 15
239000011734 sodium Substances 0.000 claims description 7
229910052708 sodium Inorganic materials 0.000 claims description 7
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
238000001816 cooling Methods 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 5
LKHYFCSSVZVVNF-UHFFFAOYSA-N ethyl hexanoate;sodium Chemical compound [Na].CCCCCC(=O)OCC LKHYFCSSVZVVNF-UHFFFAOYSA-N 0.000 claims description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
239000000126 substance Substances 0.000 claims 5
230000008025 crystallization Effects 0.000 claims 2
239000000243 solution Substances 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
239000013078 crystal Substances 0.000 description 16
239000000047 product Substances 0.000 description 11
239000000463 material Substances 0.000 description 8
OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 7
229960004659 ticarcillin Drugs 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000003981 vehicle Substances 0.000 description 6
241000786363 Rhampholeon spectrum Species 0.000 description 5
239000003085 diluting agent Substances 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 4
229940123930 Lactamase inhibitor Drugs 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000006228 supernatant Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000282414 Homo sapiens Species 0.000 description 3
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000002441 X-ray diffraction Methods 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
238000003556 assay Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
230000014759 maintenance of location Effects 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical group C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
208000035143 Bacterial infection Diseases 0.000 description 2
241000282412 Homo Species 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
208000022362 bacterial infectious disease Diseases 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000011049 filling Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
238000001694 spray drying Methods 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
-1 triethylamine Chemical class 0.000 description 2
239000003643 water by type Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
SHCFCJUJGBRSPO-UHFFFAOYSA-N 1-cyclohexylcyclohexan-1-amine Chemical compound C1CCCCC1C1(N)CCCCC1 SHCFCJUJGBRSPO-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
IYTJRMRETHPZAC-UHFFFAOYSA-N 4,4-dibenzylpiperidine Chemical compound C1CNCCC1(CC=1C=CC=CC=1)CC1=CC=CC=C1 IYTJRMRETHPZAC-UHFFFAOYSA-N 0.000 description 1
CBQYNPHHHJTCJS-UHFFFAOYSA-N Alline Chemical group C1=CC=C2C3(O)CCN(C)C3NC2=C1 CBQYNPHHHJTCJS-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
208000022274 Proteus Infections Diseases 0.000 description 1
208000011501 Proteus infectious disease Diseases 0.000 description 1
208000032536 Pseudomonas Infections Diseases 0.000 description 1
206010057190 Respiratory tract infections Diseases 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000011149 active material Substances 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000003193 general anesthetic agent Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
208000004396 mastitis Diseases 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
208000020029 respiratory tract infectious disease Diseases 0.000 description 1
238000007789 sealing Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
238000007738 vacuum evaporation Methods 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)

CA000438962A 1982-10-15 1983-10-13 .beta.-LACTAM ANTIBIOTIQUE Expired CA1210387A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US43470482A	1982-10-15	1982-10-15
US490,441		1983-05-02
US06/490,441 US4598074A (en)	1982-10-15	1983-05-02	β-lactam antibiotics
US434,704		1989-11-09

Publications (1)

Publication Number	Publication Date
CA1210387A true CA1210387A (fr)	1986-08-26

Family

ID=27030287

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000438962A Expired CA1210387A (fr)	1982-10-15	1983-10-13	.beta.-LACTAM ANTIBIOTIQUE

Country Status (5)

Country	Link
US (1)	US4598074A (fr)
AU (1)	AU2014283A (fr)
CA (1)	CA1210387A (fr)
GB (1)	GB2129429B (fr)
NZ (1)	NZ205961A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20050245498A1 (en) *	2002-05-14	2005-11-03	Shoichet Brian K	Sterically-awkward beta-lactamase inhibitors

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1004670A (en) *	1963-04-23	1965-09-15	Beecham Res Lab	Penicillins
GB1197973A (en) *	1967-04-18	1970-07-08	Beecham Group Ltd	Penicillins
GB1312891A (en) *	1971-02-17	1973-04-11	Beecham Group Ltd	Composition containing penicillin salts
US4171303A (en) *	1974-07-30	1979-10-16	Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt.	Process for the preparation of reactive penicillanic acid and cephalosporanic acid derivatives
FR2312500A1 (fr) *	1975-04-08	1976-12-24	Rit Rech Ind Therapeut	Nouveau procede de preparation de derives de penicilline et de cephalosporine
GB1578730A (en) *	1976-06-24	1980-11-05	Beecham Group Ltd	Esters of penicillin antibiotics

1983
- 1983-05-02 US US06/490,441 patent/US4598074A/en not_active Expired - Fee Related
- 1983-10-12 GB GB08327287A patent/GB2129429B/en not_active Expired
- 1983-10-13 NZ NZ205961A patent/NZ205961A/en unknown
- 1983-10-13 CA CA000438962A patent/CA1210387A/fr not_active Expired
- 1983-10-13 AU AU20142/83A patent/AU2014283A/en not_active Abandoned

Also Published As

Publication number	Publication date
GB8327287D0 (en)	1983-11-16
NZ205961A (en)	1987-03-06
GB2129429A (en)	1984-05-16
AU2014283A (en)	1984-04-19
GB2129429B (en)	1987-05-13
US4598074A (en)	1986-07-01

Legal Events

Date	Code	Title	Description
2003-10-13	MKEX	Expiry

Publication	Publication Date	Title
KR840001776B1 (ko)	1984-10-19	세프타지딤 펜타하이드레이트의 제조방법
KR0180798B1 (ko)	1999-03-20	결정성 페니실린 유도체, 그의 제법 및 용도
EP0581552B1 (fr)	1998-04-22	Hydrochlorure de triazolylthiométhylthiocéphalosporine, son hydrate cristallin et la préparation de celui-ci
DE1795188C3 (de)	1979-11-22	3-Alkoxymethylcephalosporine, Verfahren zu deren Herstellung und die diese enthaltenden pharmazeutischen Zusammensetzungen
EP0112550B1 (fr)	1990-02-07	Sels d'addition d'acides cristallins de céphalosporines et procédé pour leur préparation
EP0005830B1 (fr)	1982-09-22	Dérivés de céphalosporine, leur préparation et les compositions pharmaceutiques correspondants
CA1210387A (fr)	1986-08-26	.beta.-LACTAM ANTIBIOTIQUE
KR100236845B1 (ko)	2000-02-01	결정성 카르바페넴 유도체
CA1104139A (fr)	1981-06-30	Compositions bactericides
CA1272715A (fr)	1990-08-14	Derive antibiotique, et methode d'epuration
DE3887691T2 (de)	1994-06-09	Cephalosporin-antibiotika.
US4863915A (en)	1989-09-05	β-lactam antibiotics
KR0135979B1 (ko)	1998-04-25	모액으로부터의 항생물질 회수방법 및 그의 약학적으로 허용할 수 있는 신규한 염
RU2090567C1 (ru)	1997-09-20	Кристаллический пивалоилоксиметил (ir, 5s, 6s)-[(4r)-2-оксо-4-пирролидинилтио]-6-[(ir)-1-гидроксиэтил]-1-метил-1-карбапен-2-ем-3-карбоксилат и способ его получения
KR920003902B1 (ko)	1992-05-18	페니실린 유도체의 수화물 및 그 제조방법
US4007176A (en)	1977-02-08	Cephalosporin derivatives
EP0039967B1 (fr)	1984-10-17	Soluté d'amoxycilline, procédé de préparation et procédé pour la préparation de formes injectables de ce soluté
US4734408A (en)	1988-03-29	Crystalline cephalosporin antibiotic salts and solvates
EP0261990B1 (fr)	1993-07-28	Sel d'addition cristallin de l'acide carboxylique de céphem
SU860705A3 (ru)	1981-08-30	Способ получени кристаллической формы D-конфигурации диаммониевой соли 7 - -карбокси- -( -оксифенил)ацетамидо/-7 -метокси-3-(1-метилтетразол-5-ил)-тиометил-1-оксадетиа-3-цефем-4-карбоновой кислоты
SU925251A3 (ru)	1982-04-30	Способ получени кристаллической формы D-конфигурации полуторной натриевой соли 7 @ -/ @ -карбокси- @ -(п-оксифенил) ацетамидо/-7 @ -метокси-3-(1-метилтетразол-5-ил)-тиометил-1-оксадетиа-3-цефем-4-карбоновой кислоты
US4339575A (en)	1982-07-13	Substituted-imidazolidinyl-3-chloro-3-cephem-4-carboxylic acid
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